But I thought it was hip to be square ... March 10, 2010 2:45 PMSubscribe

How to not look like a square?

I was recently told by someone who knows me well that I appear, and have always appeared, as a total square.

This surprised me quite a bit, because I'm into a lot of "cool" things such as the music scene, indie publishing, drug culture, etc. I let my hair down and say ridiculous things, and tell loud stories, and dance. I wouldn't really mind looking like a square, except that I realize people have kind of never invited me to the really fun shit; I guess they assume I'm "not into that" because I look like a dang square.

To be honest I don't put a great deal of care in how I dress beyond basic hygiene and maintenance; I go to a very good stylist who cuts my long hair in a pretty tame, sideswept bang fashion, I have a few pairs of well-fitting jeans and khakis, and I basically wear a v-neck sweater or cardigan over a polo shirt every day. In my mind, I look something like this, but I guess to everyone else I look like a total square. My goal is for kind of a twee sophisticate look.

So, how the heck do I hip it up so that other people besides the 3 who have known me for years don't just immediately assume I'm going to narc on them? For some background info, I work in a technical field where I can basically dress how I want, I'm in my mid 20s, I have a lot of nice shoes but mostly wear old ankle boots or chucks, I wear large dorky glasses, and don't want to spend a lot of time fussing every day.

I know that in general, you can't just immediately change your whole perceived attitude with online shopping, but links to specific products that I can buy that will make me appear a little less uptight would be appreciated. I'm not aiming to look super trendy, I just don't want to be glared at in dive bars anymore =(
(anon because drugs + embarassed)

Yeah, that picture, to me, looks like "square, played for laughs." Unless you customarily carry a pipe, the irony isn't going to be apparent.

I am not sure I can advise on clothes. I wear t-shirts and jeans, occasionally with a solid-color buttondown. I've never been accused of being square, but I've also never been accused of having fashion sense.posted by restless_nomad at 2:50 PM on March 10, 2010

My goal is for kind of a twee sophisticate look.

There's a chance the twee sophistication is actually mistaken for a Banana Republic-esque "young professional" / yuppie look. You might want to dirty things up and dress down a bit. Don't be afraid to wear t-shirts and worn-in jeans and the like along with your chucks (you may want to look into threadless, possibly).posted by naju at 2:51 PM on March 10, 2010 [3 favorites]

Twee sophisticate = square to most people. I think you need to change up your desired look if you want to look less square.posted by sid at 2:52 PM on March 10, 2010

I let my hair down and say ridiculous things, and tell loud stories, and dance.

Do you possibly seem like you're trying too hard not to be a square? Cool is mainly about not really caring if you're hip or not.

In my mind, I look something like this

If that person were out in the real world and not a model, they would look like a person trying very very hard to be hip. And not knowing how. However, you say you don't put much care into how you dress, so there's some contradiction there.posted by frobozz at 2:52 PM on March 10, 2010 [1 favorite]

Accessories. Note, for example, the scarf and pipe.

Umm... this might just be a pet-peeve of mine, but polo shirts always scream "professional in a technical field who goes home to a spouse and kids after work, and sometimes gets together with the fellas on the weekends to play Cream covers". The first step would be either dressing down a bit with screen-printed t-shirts (perhaps of some of the indie bands that you enjoy) or dressing up a bit with slim-fitted button-up shirts.posted by muddgirl at 2:53 PM on March 10, 2010 [9 favorites]

The guy in that picture looks pretty square to me. In my day we'd have called him a preppy, and you can't get much more square than that. Plus, anyone who wears the same thing every day will never come off as hip-- try mixing things up a bit with some Tshirts & jeans or something.posted by InfidelZombie at 2:53 PM on March 10, 2010 [1 favorite]

Hey! It's like I'm talking to myself. Here's my take: the twee look you link to works because it's over the top. (It doesn't strike me as sophisticated, but I get what you mean.)

There are several markers that it's ironic:
- the very good quality of the clothing (note the pinstripes on the pants and the unique shoes)
- the pipe
- the scarf
- the guy being attractive and skinny. That sort of person can make anything look cool.

Just wearing khakis/jeans and a sweater don't give an impression of hip irony, but rather that you get everything from The Gap, you know? For twee, I would add some over-the-top accessories. Fred Flare style, maybe. Something silly that shows you're not taking yourself seriously. Twee people tend to pair some really bright colors together too - like a bright red cardigan over a teal blue polo.posted by Solon and Thanks at 2:58 PM on March 10, 2010 [2 favorites]

(I also agree that ditching the polos is probably a good plan.)posted by Solon and Thanks at 2:59 PM on March 10, 2010

For starters, no one has used the word "square" to describe a dork since the 50s. I have seriously never heard anyone use this word, and I'm also in my mid 20s.

But yeah, that person in the picture you linked to is a total dork. Please, please don't wear argyle. Argyle is hideous. Also, those pants have vertical stripes. Never wear vertical stripes on anything ever for any reason.posted by Lobster Garden at 3:00 PM on March 10, 2010

After posting, I think naju is right on. Kahki + polo shirt could read "cool and twee" but it's much more likely to read "yuppie professional".

Jesus, folks. If you're not in the sort of scene that goes for over-the-top twee/geek chic looks, don't comment on the fact that "that dude looks like a dork". Of course he looks like a dork. That's sort of the point.posted by muddgirl at 3:02 PM on March 10, 2010 [2 favorites]

I think its in the details (like really bright socks or shoe or really interesting shoes). And polos don't have to be dorky tech guy if they're slim-fitting. Why not dress the way you like, keep it tidy (that look doesn't come across well if the clothes don't fit well or are worn out) and glare right back at the hipsters.

Please, please don't wear argyle. Argyle is hideous.
I absolutely love a man in argyle. And glasses. To each her own.

I'm a guy who's not exactly a fashion genius - until I was 20 or so clothes were the least of my concerns. I would throw on my baggy mass-market jeans and my baggy mass-market sweatshirt and comb my hair in the morning, and that was the extent of my preparation - so take what I'm about to say with a grain of salt:

I asked my brother, who's always well-dressed, for some tips once, and he told me something that I found interesting: When it comes to style, the two things that matter most are fit and confidence.

Trendy styles change so quickly that it's insanely difficult to stay up to date with the current fad. So find clothes that you like - and make an effort to get the fit just right. And once you've made your decision, be confident. If you like the way you look, don't let anyone else force you to change, unless you want to change.

I have a funny story that you may be interested in hearing - a couple years back (probably more like a decade now; I'm not exactly sure) those beanie hats were all the rage. A few years later, John Deere hats were in style for some reason. My 60 year old father who always wore the same damn beanies in the winter and a John Deere hat in the summer suddenly started getting tons of compliments from young guys on his sense of style - apparently my dad was so out of style that he was IN style.

The ultimate point is that you have to put this into perspective. You sound like a very intelligent person who would be fun to hang out with. Five years from now, your friends aren't going to remember a damn thing about what you wore today. They will remember the good times you had and the way you were as a person, the times you sat outside drinking beer and talking about life, the experiences that you shared as young people, and the way you conducted yourself as a human being.posted by Despondent_Monkey at 3:22 PM on March 10, 2010 [2 favorites]

either embrace your squareness (recommended) or if you are really so uncomfortable with yourself, i dunno, wash your clothes less often and don't iron. "twee sophisticate" sounds to me pretty close to "uptight" which isn't far off from "square". and twee + dive bar doesn't really compute. in any case, if you really do consider these bars dives, then you probably shouldn't go there, and that explains the looks.

it's a bit telling that you're initial reaction is that you think you will have to fuss more. you sound like you already fuss a lot about your look. fuss less.

finally, you said both "dang" and "heck". that's fine, you should really use whatever words you like, but just know that most people consider these words pretty hokey. i would say don't modify the way you speak, just be aware that some (most) people might think it sounds hokey. and if you do stay comfortable talking that way but with the knowledge of how it comes across, you might smoothly transition from an embarrassing to an endearing hokey.posted by molecicco at 3:24 PM on March 10, 2010 [1 favorite]

I pretty much dress like Queen Elizabeth when she's on vacation in Scotland, which is precisely why I like to wear a leather cock ring as a bracelet sometimes.

I like Lord Whimsy's distinction: bohemianism disregards rules that mainstream society can't afford to ignore, and dandyism follows rules that mainstream society can't afford to observe. It seems like you are attempting to be a dandy (whether you are succeeding is another question), and this is generally not accepted as cool.

Lots of people in the 'cool' crowd are pretty narrow-minded. They pretend not to be, but nonconformity is coded, and they don't like it when you play in the margins. It's too subtle, and hanging out with you puts them at risk of looking like they hang out with squares, even if they know you aren't.posted by AlsoMike at 3:47 PM on March 10, 2010 [9 favorites]

And here I was thinking that pic was of a very very butch woman. Sheesh.

Actually I am thinking that it isn't your clothes; it's probably how you come across-how you WEAR what you wear.

I know I used to come across back in the day as "rich girl goodygoody" which was so very inaccurate it was hysterical-me in my thrift store clothes and 99 cent earrings which for some reason people thought were diamonds. Trust me, it wasn't what I wore. (And yes, back in that day I was into all sorts of things that present day me would be horrified at, so the fact people perceived me as Miss Innocent was quite puzzling.)posted by St. Alia of the Bunnies at 3:50 PM on March 10, 2010 [1 favorite]

Anonymous, this entire question screams to me, "I try too hard!" You say that you're surprised you appear to be square specifically because you do "cool" things like the music scene, indie publishing, drug culture, etc other cool things you're doing. You're always saying ridiculous things, telling loud stories, and dancing. But doing that stuff alone isn't what makes anyone cool. It's their attitude and how they carry themselves. People might just think you're kind of annoying and that might be more of a reason why they don't invite you to things. Your clothes might merely be a symptom of a larger issue people have with how you conduct yourself. One way to find this out is if you try inviting them out to the really fun shit, instead of wondering why they aren't inviting you. If everyone still avoids you even if you are actively trying to socialize with them, you might have your answer.

But let's say that might not be the case. And don't take any of that personally because obviously I don't know you, and I'm only going by what you say in this question. As someone who has worked in industries where dressing slovenly is normal and accepted, I know that any young guy who dresses somewhat above that level of slovenliness is going to look kind of like a square. Based on your description of yourself, you look and sound like someone who puts a lot of thought into his wardrobe and appearance, trying to maintain some sort of "image." A lot of people in technical fields don't give a crap about what sort of image they have in regards to what they wear; they just want to be comfortable and talk about stuff that interests them. If you focus more on dressing for comfort rather than fashion you may find their perception of you to change.

If you are truly comfortable in the clothes you are already wearing and aren't only wearing them because you thought that was a look people would find cool, maybe those people just aren't the kinds of people you want to hang out with anyway. Be yourself and you'll find your crowd.posted by wondermouse at 3:53 PM on March 10, 2010

Also, those pants have vertical stripes. Never wear vertical stripes on anything ever for any reason.

My husband is a square*, and he wears polo shirts with khakis or button-down shirts with sweaters over them. And he's 43.

So you are maybe dressing a little older than you should be, and definitely more conservatively than someone cool needs to be.

Don't go with cardigans. Cardigans on a guy say sweet Mr. Rogers, and on someone young they give off an affected, trying-too-hard air. Get yourself a nice, functional leather jacket or something. If you really want to go sophisticated and twee, find a vintage tweed blazer to wear over your clothes.

Replace the button-downs and polos with comfier shirts, henleys or tees. If you feel too casual in that, than ask the friend who says you're square what he would recommend, or just obseve him and use him as a jumping-off point for your own style.

*It's okay, he really is and it's his choice. He hasn't changed his hairstyle or the way he dresses in 20 years. I've managed to get him to wear brighter colors anyway.posted by misha at 3:58 PM on March 10, 2010

Are you male or female? You describe long hair with sideswept bangs, which sounds like girl hair, but link to a picture of a man. Maybe I'm being too literal, but I'm confused.posted by chesty_a_arthur at 4:05 PM on March 10, 2010

I wear large dorky glasses

Are they dorky in a somewhat ironic sense, or just regular dorky? Because I find that unintentionally bad or generic glasses ruin nearly any outfit.posted by ripley_ at 4:12 PM on March 10, 2010

You can't go wrong with a pair of these truly heroic golf pants, also worn by the Norwegian curling team. People will be electrified when they see you, and say to themselves, "There goes a man who is truly alive!"posted by AlsoMike at 4:16 PM on March 10, 2010 [5 favorites]

I once wandered into my favorite dive bar after a wedding, dressed to the nines. People glared at me. I went to the bar and bought a pitcher. Took it to an empty patio table along with three empty glasses.

you describe long hair with sideswept bangs, which sounds like girl hair, but link to a picture of a man.

Depending on your definition of "Long," that's my hair. And I'm definitely a guy. And I'm definitely never mistaken for a girl. A much younger guy, yes, but never female.posted by Tomorrowful at 4:34 PM on March 10, 2010

Here's what you shouldn't do:
Wear khakis
Wear pique polos (this means the thicker stretchy texturey material)
Wear clothes that are as un-form fitting as a middle-aged golf dad would wear (this means wear them tight, or if you don't like that, wear them extra loose, maybe)

Things you should wear if you want to look more "indie"
Plaid
Jeans that are tightish and dark wash or light wash, not true blue
Corduroy
Polos made of soft cotton, OR vintage-style Pengin/Munsingwear-style ones that are tighter or have accent trim. These are made of a much thinner pique material than the ones you find in stores todayposted by ishotjr at 4:38 PM on March 10, 2010 [3 favorites]

Tomorrowful, thanks-- I was picturing shoulder-length, you know, girl hair. On a girl. I think it was the phrase "sideswept bangs."posted by chesty_a_arthur at 4:44 PM on March 10, 2010

Your GOAL is "twee sophisticate"?

That's so hopelessly square it wouldn't roll off a pitched roof.

I am the least cool person you will ever meet, and I will now tell you how to be cool: stop trying.posted by BitterOldPunk at 4:51 PM on March 10, 2010 [6 favorites]

Personally, I would look for other friends. Either that, or have this friend of yours go shopping with you, if s/he is such an expert.

If I understand you correctly, it seems as though only one person has declared you to be a "square". It seems to me that a really good friend, who was deeply concerned that you had been missing out on years and years of "really fun shit", would have 1) delivered this news in a much kinder way, and 2) given you some examples of what s/he is talking about, and tips, hints, help, etc. to help you reveal the truly hip person you really are inside. This, of course, is assuming that your friend knows what s/he's talking about. As Lobster Garden points out, the use of the word "square" does not seem to support the idea that your friend is the next Tim Gunn. I am deeply suspicious that this person is simply being cruel, or thinks it's funny to set you spinning this way.

Also, how do you know that you are missing out on "really fun shit", if you're not there? I'm wondering if you're worrying too much about this. . .posted by cookiesncream at 5:01 PM on March 10, 2010

If you were an adolescent male in the mid-1970's, nobody at high-school would smoke-up with you.

You are not an adolescent male in the mid-1970's.posted by ovvl at 5:11 PM on March 10, 2010

Seconding wondermouse and others: The problem is that you give a shit and it shows. That's the whole thing about coolness--it can't look like you're trying.

It's not your clothes. It's the fact that when somebody tells you you look like a square you get worried about it, instead of knowing they don't know what they're talking about. Coolness is not only about confidence but, in many ways, conceit.

Don't sweat it so much. When you do, you start to get on a treadmill of self-doubt and introspection that doesn't work, because that self-doubt and introspection is exactly the problem.

Note: I'm not trying to advocate being a conceited jerk. This is all very superficial social advice that (I like to think) doesn't reflect much on your actual character.posted by ropeladder at 5:21 PM on March 10, 2010 [1 favorite]

I'm neither a hipster nor a boy but I know what those dudes dress like and khakis and polo shirts are not it. Khakis and polo shirts are for people who must wear them (dress code wise) or choose to wear them because they don't give a shit. (Which is fine - maybe more fine than caring, even! But that's not the question at hand). For shirts you want button down or T - and for pants you want jeans, cords, flat front narrow trousers (but absolutely never ever khakis).posted by moxiedoll at 5:36 PM on March 10, 2010

follow-up from the OP

could you please let people know that i am female, that i don't think being a dork who is interested in music and weed is some kind of ridiculous, fabricated personality type; that i let my hair down in appropriate situations (wild party) and am generally kind of a quiet, typical nerd; that i have and keep friends who DO invite me to any event, but acquaintances really only invite me out for book readings or techie meetups and sound surprised when they later found out i totally dig $n activity--and this is why i am asking how to appear less square?

1. When I meet someone I sort of do a mental size up in my head "would I hang out with this person?" Sometimes it's subconscious, sometimes I'm aware of the subconscious impulse. I would not hang out with the person in that picture because either he a) really is a square & doesn't realize/care or b) is doing it ironically, and that's even worse. Before you judge me for judging you, realize that prejudice goes deep & is more subtle than we may have previously realized. I'm from Working Class Brooklyn & figure I'll get a long with other working class Brooklynites. That's just the way it goes.

2. I'm also pretty square. I enjoy spending quiet evenings at home with my girlfriend & don't really get invited out for shenanigans. It used to bug me, but now, I don't really care, plus my friends (both old & new) aren't really the type that go out for shenanigans anymore. Still, it was always interesting that they'd censor their stories around me because they'd assume I was judging them.

3. If you want to slowly improve the way you look, play the same mental game I do. When you see someone on the street that looks the way you want to, make note of what it is about them that you like. When you go shopping, keep that mental image in your head & don't buy anything lesser than that. "Would that dude buy this?"

4. When you go shopping, get the shop staff to help you. Nothing changes your look faster than having someone else pick your clothe out for you & since you're doing the actual buying, it's not like you're relinquishing control. (hint: shop in places where the shop staff looks like the kind of person you're aspiring to dress like)

5. Have you considered that it's not your clothes, but your demeanor? Try podcasting on for a spin. I downloaded this new show on the PS3 playstation called The Tester about gamers who want to be testers for Playstation - a typical reality show elimination type thing. OH MY GOD the geekery. WOW. Seriously, those guys were just pure 100% dork. I could see some of myself in them (which is scary) but thankfully I'm not a bad - at least I don't think so, how am I to know? All I know about what others think of me is what they let on, and they could just be polite.

Check out a podcast like You Look Nice Today and figure out which of the guys in the podcast are cool, and which are the poor put upon geeks. And make your own podcast and see what you sound like on recording. Record yourself interviewing someone else. If you sound like This Podcast (I listened to the one with Eric Zimmerman - it was painful), then you may need to work on more than just your clothes.posted by MesoFilter at 6:12 PM on March 10, 2010

Since you're female stop wearing polo shirts and cardigans.

Barring that or not, several have mentioned one incongruous item, or the details. This is exactly right, as I doubt you want us to give you a hipster costume to wear.

Maybe a tattoo? There are even printable temporary tattoos and I'm actually currently sporting a large Gonzo fist on my arm. I'm pretty sure I could dress in pleated khakis with a tucked in Lacoste shirt without being in any danger.

A patch of dyed hair seems to be code for, "No, really. I'm cool." Also maybe do lots of different things with your hair. A side-ponytail one day, Pocahontas braids the next.

Are your glasses red or tortoise shell or something? That'd help.

Over the top shoes. Cowboy boots. Red vinyl.

It doesn't matter really. It'll be better if it's something you think up.posted by cmoj at 6:17 PM on March 10, 2010 [1 favorite]

It doesn't matter what you wear. You need confidence.

I realize people have kind of never invited me to the really fun shit

There is no really fun shit, even parties, your friends may be inviting you to things they think may interest you. If you want to go t a party, say "Aren't there any parties we could go to? I don't want to go to a poetry reading tonight."

YOU make shit fun, not the other way around.

Oh I love argyle too, on ANYONE.posted by Max Power at 6:23 PM on March 10, 2010

Well, I think you answered your own question. You said you are generally kind of a quiet, typical nerd. So no one is going to know that you're interested in other things unless you tell them. If you want to be invited to indie concerts, then wear indie band t-shirts. Or talk about indie bands.

Also, three things:
1. Polo shirts are the single uncoolest thing on the planet.
2. True coolness is achieved when you don't actually care what anyone thinks of you. So wear your polo shirts proudly, and live your life.
3. You are in your mid-twenties; therefore, it's absolutely guaranteed that no matter what you do now, when you are 34 you will look back at your current self and be mildly-to-horribly embarrassed by what you did/said/wore. Your 20's are about trying things out and finding yourself. Have fun and don't worry about it.

But if you don't care about any of that and just want some specific advice, then just get yourself some of those (politically incorrect) American Apparel shirts, and some outrageously expensive jeans that are designed to look like you pulled them out of the dumpster, and be done with it. And remember that the less you look like you care, the cooler you appear to be.posted by MexicanYenta at 6:27 PM on March 10, 2010 [1 favorite]

Yeah, I think you might have thrown people with the pipe-smoking gent, there. (Confidential to everyone: I TOLD YOU IT WAS A LADY!)

Look, I have not been cool for between 8 and 10 years, so I am not an authority, but I think that losing the polo shirts might help. Polo shirts on women do not say "I am a dork who's into weed and indie rock," for whatever reason.

Eh, if you start to put too much care in how you dress, those people you are worried about will call you worse things than "square". Dress like a man and don't worry about portraying a certain style unless you want to get into the cosplay scene.

Beyond that, just project who you are and don't do it in a meek way. Be up front, confident, and don't try to be someone else. If everything else fails, don't worry about what some moron you don't know thinks about you based on how you dress. They are the type of people you really shouldn't be trying to impress.posted by JJ86 at 6:34 PM on March 10, 2010

Um, I hate to say this, but it sounds like you dress like a middle aged suburban mom who never grew out of her preppy high school phase. (I am a middle aged suburban mom, and my college age daughter glares at me when I dress like that.) It's fine, if that's the look you want, but you will never *ever* look "twee sophisticate" dressing like that.

You want more "indie" cred? wear a skirt. Not a suit skirt, a full flowy skirt. With the chucks or ankle boots and polo and/sweater combo. Wear an untucked slim-fitting buttondown shirt under your sweater with the khakis. Put a funky hair accessory in your hair. Get smaller framed dorky glasses. Wear fitted polos, not loose ones. Don't match colors.

Attempt to not look like a Sears or Coldwater Creek ad. (which is not to say that you won't find good pieces there, but don't wear them together -- CC has some fairly nice skirts.)posted by jlkr at 6:35 PM on March 10, 2010 [3 favorites]

Rather than yammer on for a while like I usually do, let me give you a few things to start with, and see where it goes:

1. Most of the time you're quiet and formal, only occasionally letting your hair down for wild parties. Switch that around; let your hair down all the time, and save quiet and formal for those situations that require it.

2. Switch your clothes to something you like to look at on other people, but would *never* wear yourself. Lose the sweaters and pants, and get some skirts and dresses and shorts. Even the most together person can benefit from the perspective shift that a new type of outfit brings. Start with a few, and grow from there.

3. Keep on singing and doing all those other things you enjoy, and try to cultivate an attitude that allows you to stop caring if someone calls you a square -- because if you are, that's who you are, and what the hell is wrong with that, anyway?

Above all, do whatever it takes to allow yourself to be yourself, no matter what other people think or what you think they'll think. Allow yourself to be wrong, allow yourself to be awkward and ugly, allow yourself to be yourself authentically and completely. Some of your friends will leave, and you'll make new ones that are better suited to the you inside.posted by davejay at 6:38 PM on March 10, 2010

Oops, new info about OP being a chick invalidates the first part of my response but the second part still stands. Don't be afraid to be assertive which works for either sex.posted by JJ86 at 6:40 PM on March 10, 2010

Any time you take a stand on something, without playing it neutral and safe,you'll get a lot of people who won't like it. Since you were trying for something, had a dressing strategy of sorts, it was open to criticism. So it was only inevitable.

Most advice you get in a public forum will be mainstream consensus. Is that really what you want? That includes hip mainstream consensus, possibly the worst of all.

There are many forms of irony, to use that dratted word again, and many different sartorial wavelengths so to speak, and I'm guessing that your friend just couldn't pick up on your frequency. One of my nieces once told me with nothing but good intentions that I should go shopping for some better clothes --at the Gap. One of my coworkers once hinted that I should stop wearing thrift store clothes and get some nice designer jeans. These are just examples, you get the idea.posted by Rich Smorgasbord at 6:52 PM on March 10, 2010

Have you ever considered you might be the hipster and they might be the nerds? Lots of dipshits are into "cool" things. I mean, look at the wide range of different types of assholes who like weed. Tons of losers, and pot is cool as shit.posted by mckenney at 6:56 PM on March 10, 2010

Yikes, people are judgmental. Don't feel bad for wanting to change your style up a little because you're being perceived in a way you dislike.

Maybe try to avoid going for any particular style for a little while? Pick up some fitted t-shirts simple blouses or cute button-up shirts. It's a bland American Eagle style, but it won't signal anything particularly positive or negative. Pair them with jeans, wear some accessories maybe. You can still wear your other clothes, but maybe not to dive bars and parties.posted by Solon and Thanks at 7:02 PM on March 10, 2010

So this might be sort of offensive... but maybe you should stop dressing like a boy. Not that what you're currently wearing is wrong, or anything, but I think it's telling that people in this thread ignored the long hair and assumed you were a guy based on your wardrobe. The hipster-indie girls I see around (at college and at home and on the internet) wear a lot of skirts, a lot of vintage, a lot of ironic cheap accessories. Etsy has this sensibility, Wardrobe Remix on flickr has a lot of pictures of real people dressing this way and listing what they're wearing and where they got it, and hey, even Urban Outfitters could maybe help you out.

If you're a girl and you wear jeans or khakis and polos or sweaters all the time, yeah, maybe you could look like the girl?/guy in the picture you linked to and do the whole genderqueer-y thing, but you'd need to be able to pull it off- by being more confident, by having nicer clothes that fit you better and are many steps up in quality and style from Gap/Banana Republic standard stuff, and by accessorizing a lot. You could accidentally be dressing like a sensible grad student who hasn't bought any new clothes in six years, by wearing generic stuff that doesn't fit well.

Finally, though, it sounds like changing how you dress isn't necessarily going to get you the results you want. I understand where you're coming from- I like indie things too but I'm not cool in that way, and I know it's mostly the result of a lack of self-confidence and the many details of how I present myself that have nothing to do with what I wear. You can get an entire new wardrobe- but you're liable to discover that you're still the same person in the same situation in different clothes.posted by MadamM at 7:26 PM on March 10, 2010 [1 favorite]

Ok, this is easy:

Stop spending so much money on your hair. Stop spending so much money on your appearance, period. Start getting your hair cut at supercuts (or cut it yourself) and start shopping at thrift stores. Don't wear ankle boots. Wear sneakers--chucks are a start, but also consider bright, flashy retro sneakers like Onitsuka Tigers--or tall boots. Cowboy boots or riding boots will do the trick. Consider wearing tall socks, too. Nothing says fun like tall socks! Stop wearing khakis. Stop wearing khakis. Also, no more v-necks or polos. These are middle-aged lady clothes and they're bad bad bad. Buy a few really cute, really pretty sundresses--maybe something vintage off etsy and some nice skirts--no longer than calf-length. Buy some funky accessories. Cool headbands or scarves, funky jewelry. None of this has to be expensive; I buy most of my accessories at forever 21. Consider doing something wacky that you've always wanted to do: get a tattoo or a piercing or dye a big chunk of your hair a funky color. In fact, don't be afraid to mess up your hair a little. I can always tell the girls that are prissy deep down by how much their worry about their hair and ruining it. Get jeans that are a little baggy on you. Cut some of your jeans into long cut-off shorts this summer. When it's cold, wear them with tights or long johns and an ancient pair of doc martens. Be a little messier. Buy some funky plastic eyeglass frames online without trying them on first. Have fun with eyeshadow but don't worry too much about foundation. Listen to Tullycraft. Think about how the girls in their songs must look: cool, with flashes of fashion brilliance, but off-kilter, a little grubby; unafraid to take risks. Mostly, stop worrying, and start seeing your appearance as an adventure.

At least, that's what I do, and, at first glance, people tend to think I'm way more exciting than I am.posted by PhoBWanKenobi at 7:28 PM on March 10, 2010 [3 favorites]

You know about The Sartorialist, right? I'm not sure what the dressed down version of that is, but I bet if you tried to dress that way by shopping at thrift stores, you'd come pretty close.

Also, in my circles, the secret sign for "I'm cool" is the bike helmet. Also, smiling. In fact, the people in my office that I'd invite out for music are the ones that I suspect have this super-secret fun life because they're happy.posted by salvia at 8:05 PM on March 10, 2010 [1 favorite]

Polo shirts (esp. on a woman) and khakis scream "square" to me. But I would disagree with other posters who have said not to wear argyle or cardigans.

If you're willing to wear skirts, then knee-length, a-line skirts look on most body shapes (esp. short "twee" types).

Non-clothing ideas: get a more indie haircut, dye your hair (or a chunk of it), get a tattoo, try to wear more interesting/daring jewelry.

Yeah, this question sounded like it was coming from a guy. I was imagining a guy who dressed like that and had long hair and glasses, talked really loud, said ridiculous things, danced, and generally annoyed the hell out of me. I have seen guys who dress like that and have long hair and glasses and also occasionally act like that, so it wasn't unlikely.

Your being a girl puts things in a different light, somehow, but I find it interesting that you dress so much like a man that you actually linked to a picture of a man when giving an example of the clothing you wear. I hope you understand why a lot of us thought you were a guy.

My overall conclusion remains the same, though: in general, wear what YOU are comfortable in, and invite people you want to hang out with to things you'd like to do with them, which will cause them to associate you with those things.

Judging by the crowd you're looking to appeal to (dive bars etc), I think Urban Outfitters would be a good place for you to start. The V-neck-over-polo-shirt-with-khakis look is very preppy and not something I'd associate with hipster cool on a girl. It's not a bad look for work, but given your workplace it certainly sounds like you can stand to look less formal if you'd like to get involved with the indie crowd.posted by wondermouse at 8:52 PM on March 10, 2010

If you are uncomfortable with dressing girly, don't do it. There is nothing more awkward than trying to stuff yourself into a gender expression that feels wrong to you.

The combination of long hair and unfemmey clothes strikes a lot of people as conservative, even prudish. On the other hand, if you had a similar hairstyle to the man in the picture, I'd assume you were a lesbian, not a dork (note: I am a lesbian). A very short haircut in a bright color would look more fun than long hair, though you might break a few hearts if you aren't into the ladies.

Wear fitted t-shirts (the american apparel has them and it's like.. roll your eyes at how hipster it is & shop there anyway.. places like gap and jcrew and such are ok.. banana republic is not cool) instead of polo shirts. and dark jeans, regular straight cut if they suit you, maybe a higher waisted if they suit you. Cardigans are great and if you want to be tweeish about it.. fitted cardigans that button all the way to the neck, maybe with 3/4 sleeve, or cable knit. Search etsy for vintage cable cardigans.

What about the glasses? Some kinds of large dorky glasses are cooler than others. Maybe don't wash your hair so much or at least don't have it look like you spent $$$ to have it professionally blown out.

Also, it's been my observation from being at more than a few indie scene type of shows & hip dive bars and such.. there is a color palette thing going on. Black, dark navy, olive green, cranberry, chocolate brown, high-contrast primary colors, white. While colors like.. dusty pink, soft teal, celery green, khaki, stuff you'd see in office-appropriate stores.. those are often out of place.

I agree with those who say it's like.. shrug and act like you don't care if you're cool. Some cool cool indie music people glare at everyone anyway. They just do. But I also feel you on being aware that it's easier to act this way if you're dressed to fit in pretty well, and harder if you feel like you don't. Liebemarlene Vintage is some good indie type style inspiration and she has a shop, too - I recommend.posted by citron at 9:18 PM on March 10, 2010 [2 favorites]

I'm surprised no one has mentioned hoodies. A hoodie with a pair of semi lowrise jeans and some flat pull on sneakers will not make you look square.

Just be yourself and be confident in yourself, though. People are surprised about facets of my personality all of the time, and to be honest, I'm surprised by aspects of other people all the time. It's part of getting to know someone and part of what makes people interesting. I'd rather find out those things through getting to know someone and not because they are wearing something specific.posted by k8lin at 9:28 PM on March 10, 2010

Ack! I'm so sorry for assuming you were a guy. The pic you linked threw me.

I still think you are dressing like someone much older, and not in a sophisticated way but in a carpooling Mom kind of way. And I AM a carpooling Mom, so you can believe me when I say that.

Still saying dump the cardigans and the polos. I think, if I were you, I'd hit vintage stores for dressier times and go for indie band tees for everyday casual. At work, citron has hit on something here: black and white and jewel tones or fall tones seem to scream young while pastels, again, look dated.

And, as I said, ask the friend who so kindly pointed out the squareness for suggestions, or follow friend's lead if you want the same invitations.posted by misha at 9:30 PM on March 10, 2010

As a guy I'm no longer sure if I can help out, but this girl strikes me as someone who is twee in a cool, laid-back, feminine way. PhoBWanKenobi's advice also seems pretty good.posted by naju at 9:30 PM on March 10, 2010 [1 favorite]

Emulate people you think look especially good. Read Vice DOs and DON'Ts and Street Boners and steal ideas from there as needed (both generally NSFW). Eventually you'll be fine. Good luck!posted by ripley_ at 9:38 PM on March 10, 2010

I tattoos running up and down my arms and metal shot through various parts of my face. I used to dress pretty outrageously, but lately have taken to wearing solid color polo shirts and plain black work pants. Some people might think I look like an asshole, but I'm pretty sure no one ever thinks I look like a square.

Tattoos are probably a bit drastic for what you're talking about, but have you considered getting a lip ring? They look great and it will dramatically change the way people perceive you without requiring an overhaul of your entire wardrobe.posted by 256 at 9:41 PM on March 10, 2010

I'm surprised no one has mentioned hoodies. A hoodie with a pair of semi lowrise jeans and some flat pull on sneakers will not make you look square.

It won't make you look square, but it will likely make you look very young, and not in a good way.posted by thisjax at 11:14 PM on March 10, 2010

thisjax, the OP is in her mid-20s. I'd say that is a fine age for hoodies, jeans, and sneakers. My friends wear these all the time and are in their late 20s or early 30s; no one accuses them of looking very young. Maybe the OP should be trying to look younger given her age, since she is young. A hoodie is certainly less drastic than a tattoo or a lip ring.

You can also buy cashmere or velvet hoodies, which look more sophisticated than a simple cotton one. An indie band tee will always look young in a way that carefully selected hoodies will not.posted by k8lin at 11:57 PM on March 10, 2010

1. Khakis = Chinos right? they are the first problem. did you buy them at Gap? they are just boring and MOR/Square. - go for quality or vintage wool trousers or corduroy.

2. polo shirts.. are no longer cool as the Alt-Edge of the ironic PoloShirt has already been co-opted by mainstream culture.
try bottoned colared shirts instead. and again the only way to avoid MOR / Squareness is with Vintage or quality small designer label stuff.posted by mary8nne at 5:40 AM on March 11, 2010

The picture you posted of "I think I look kinda like this?" That person looks square.

If you're wearing cardigans over a polo shirt with big dorky glasses, unless you're hanging out with hipsters who live and breathe irony at the moment, yeah, you've already typecast.posted by talldean at 5:59 AM on March 14, 2010

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